# US 7,608,563 B2 · 3-phenoxy-4-pyridazinol derivatives and herbicide composition containing the same

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- Number: US 7,608,563 B2
- Document ID: US7608563B2
- Status: Granted
- Kind: B2
- Application number: 10/487,013
- Filed: 2002-08-14
- Published: 2005-02-17
- Granted: 2009-10-27
- Earliest claimed: 2001-08-17
- Assignees: Mitsui Agro Chemicals, Inc.
- Inventors: Yoshihisa Tsukamoto; Hiroyuki Komai; Junji Kadotani; Kiyoshi Koi; Shigeru Mio; Hideo Takeshiba
- Web page: https://patentgrep.com/patent/US7608563B2

## CPC

- C07D 401/12: linked by a chain containing hetero atoms as chain links
- A01N 43/58: 1,2-Diazines; Hydrogenated 1,2-diazines
- C07D 237/16: Two oxygen atoms
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- C07D 417/12: linked by a chain containing hetero atoms as chain links
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## Abstract

A compound represented by the formula: [wherein R1 represents a hydrogen atom, a halogen, atom, alkyl group, etc., R2 represents a hydrogen atom, a halogen atom, alkyl group, etc., R3, R4, R5, R6 and R7 each independently represent a hydrogen atom, a halogen atom, a substitutable alkyl group, a substitutable alkenyl group, alkynyl group, a substituteable cycloalkyl group, etc., or R3, R4, R5, R6 and R7 may form a ring which may be substituted, which is formed by the adjacent two of them with carbon atoms to which the respective substituents are bonded, m and n each independently represent 0 or 1.] a salt thereof, an ester derivative thereof and an agricultural chemical containing the same as an effective ingredient, and a herbicidal composition containing the compound and a second herbicidally active compound as effective ingredients.

## Claims

### Claim 1

A compound represented by the formula:
wherein R1 is a chlorine atom or a bromine atom,
R2 is a hydrogen atom,
R3, R4, R5, R6 and R7 each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a C1 to C4 alkyl group, a C3 to C4 cycloalkyl group, a cyano group, a C2 to C3 alkoxycarbonyl group, a nitro group, a C1 to C3 alkoxy group or a trifluoromethoxy group, or R3, R4, R5, R6 and R7 are a group represented by —CH2CH2CH2—, —CH(CH3)CH2CH2—, OCH2CH2, —OCH═CH— or
which is formed by two adjacent members of R3, R4, R5, R6 and R7, provided that R3 is not a hydrogen atom, and m and n are both zero, a salt thereof or an ester thereof.

### Claim 2 (depends on 1)

The compound, a salt thereof or an ester thereof according to claim 1, wherein R1 is a chlorine atom.

### Claim 3 (depends on 1)

The compound, a salt thereof or an ester thereof according to claim 1, wherein R3, R4, R5, R6 and R7 each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a C1 to C3 alkyl group, a C3 to C4 cycloalkyl group, a cyano group or a C1 to C2 alkoxy group, or R3, R4, R5, R6 and R7 are a group represented by —CH2CH2CH2— or —OCH═CH—, which is formed by two adjacent members of R3, R4, R5, R6 and R7, provided that R3 is not a hydrogen atom.

### Claim 4 (depends on 1)

The compound, a salt thereof or an ester thereof according to claim 1, wherein R1 is a chlorine atom, R3, R4, R5, R6 and R7 each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an isopropyl group, a cyclopropyl group or a methoxy group, or R3, R4, R5, R6 and R7 are a group represented by —CH2CH2CH2—, which is formed by two adjacent members of R3, R4, R5, R6 and R7, provided that R3 is not a hydrogen atom.

### Claim 5 (depends on 1)

The compound according to claim 1, wherein the compound is selected from the group consisting of 6-chloro-3-(2-iodophenoxy)-4-pyridazinol, 6-chloro-3-(2-methyiphenoxy)-4-pyridazinol, 6-chloro-3-(2-cyclopropyiphenoxy)-4-pyridazinol, 6-chloro-3-(2,3-dihydro-1H-inden-4-yloxy)-4-pyridazinol, 3-(1-benzofuran-7-yloxy)-6-chloro-4-pyridazinol, 6-chloro-3-(2-methoxy-5-methylphenoxy)-4-pyridazinol, 6-chloro-3-(2-chloro-6-cyclopropylphenoxy)-4-pyridazinol, 3-(2-bromo-6-methylphenoxy)-6-chloro-4-pyridazinol, 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol and 6-chloro-3-(2-cyclopropyl-3,5-dimethyiphenoxy)-4-pyridaziflol, or a salt thereof or an ester thereof.

### Claim 6 (depends on 1, 2, 3, 4, 5)

The ester of the compound according to claims 1, 2, 3, 4 or 5, in which a group bonded to the oxygen atom of the hydroxyl group at the 4-position of the pyrazine ring is a C2 to C4 alkylcarbonyl group; a benzoyl group which is unsubstituted or substituted with a methyl group or a 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yloxycarbonyl group; a 1-azetidinylcarbonyl group; a 4-morpholinylcarbonyl group; a C2 to C3 alkoxycarbonyl group which is unsubstituted or substituted with 1 to 3 chlorine atoms; a dimethylcarbamoyl group; a methoxy(methyl)carbamoyl group; a C1 to C3 alkylsulfonyl group which is unsubstituted or substituted with 1 to 3 fluorine atoms; or a phenylsulfonyl group which is unsubstituted or substituted with a chlorine atom, a methyl group, a 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yloxysulfonyl group or a nitro group.

### Claim 7 (depends on 1)

The compound or a salt thereof or an ester thereof according to claim 1, wherein the compound is 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-methylbenzoate.

### Claim 8 (depends on 1)

The compound or a salt thereof or an ester thereof according to claim 1, wherein the compound is 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl dimethylcarbamate.

### Claim 9 (depends on 1)

The compound or a salt thereof or an ester thereof according to claim 1, wherein the compound is 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 1-propanesulfonate.

### Claim 10 (depends on 1)

The compound or a salt thereof or an ester thereof according to claim 1, wherein the compound is 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-methylbenzenesulfonate.

### Claim 11 (depends on 1)

The compound or a salt thereof or an ester thereof according to claim 1, wherein the compound is 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-morpholinecarboxylate.

### Claim 12 (depends on 1)

The compound or a salt thereof or an ester thereof according to claim 1, wherein the compound is 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 1-azetizinecarboxylate.

### Claim 13 (depends on 1)

The compound or a salt thereof or an ester thereof according to claim 1, wherein the compound is 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl benzenesulfonate.

### Claim 14 (depends on 1)

An agricultural chemical composition which comprises the compound, a salt thereof or an ester thereof according to claim 1 as an effective ingredient in combination with a carrier.

### Claim 15 (depends on 1)

A herbicidal composition which comprises (i) a herbicidally effective amount of at least one 3-phenoxy-4-pyridazinol compound selected from the group consisting of the compound, a salt thereof or an ester thereof according to claim 1, and (ii) a herbicidally effective amount of at least one herbicidally active compound selected from the group consisting of 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-pyrazolyl-p-toluenesulfonate, 2-[4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yloxy]acetophenone, 2-[4-(2,4-dichloro-m-toluoyl)-1,3-dimethylpyrazol-5-yloxy]-4′-methylacetophenone, 5-cyclopropyl-1,2-oxazol-4-yl α-α-α-trifluoro-2-mesyl-p-tolyl ketone, 2-(2-chloro-4-mesylbenzoyl)cyclohexan-1,3-dione, 2-(4-mesyl-2-nitrobenzoyl)cyclohexan-1,3-dione and 4-chloro-2-(methylsulfonyl)phenyl 5-cyclopropyl-4-isoxazolyl ketone.

### Claim 16 (depends on 15)

The herbicidal composition according to claim 15, wherein the herbicidally active compound is 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-pyrazolyl-p-toluenesulfonate.

### Claim 17 (depends on 1)

A method for killing weeds comprising applying to weeds or a locus thereof a herbicidally effective amount of the compound, a salt thereof or an ester according to claim 1.

### Claim 18 (depends on 15)

A method for killing weeds comprising applying to weeds or a locus thereof a herbicidally effective amount of the composition according to claim 15.